Abstract
Flavonoids and carotenoids with rich structural diversity are ubiquitously present in the plant kingdom. Flavonoids, and especially their glycosides, are more hydrophilic than most carotenoids. The interaction of flavonoids with carotenoids occurs accordingly at water/lipid interfaces and has been found important for the functions of flavonoids as antioxidants in the water phase and especially for the function of carotenoids as antioxidants in the lipid phase. Based on real-time kinetic methods for the fast reactions between (iso)flavonoids and radicals of carotenoids, antioxidant synergism during protection of unsaturated lipids has been found to depend on: (i) the appropriate distribution of (iso)flavonoids at water/lipid interface, (ii) the difference between the oxidation potentials of (iso)flavonoid and carotenoid and, (iii) the presence of electron-withdrawing groups in the carotenoid for facile electron transfer. For some (unfavorable) combinations of (iso)flavonoids and carotenoids, antioxidant synergism is replaced by antagonism, despite large potential differences. For contact with the lipid phase, the lipid/water partition coefficient is of importance as a macroscopic property for the flavonoids, while intramolecular rotation towards coplanarity upon oxidation by the carotenoid radical cation has been identified by quantum mechanical calculations to be an important microscopic property. For carotenoids, anchoring in water/lipid interface by hydrophilic groups allow the carotenoids to serve as molecular wiring across membranes for electron transport.
Highlights
Flavonoids and carotenoids are naturally occurring pigments ubiquitously present in the plant kingdom and in other types of photosynthetic organisms, playing important roles in light harvesting, photo-protection and antioxidation [1,2]
Transformation of different puerarin radicals in the isoflavonone backbone occurred fast and was found independent of the concentration of parent molecules, and proposed to result from intramolecular electron transfer. Such remarkable intramolecular electron transfer of isoflavonones may explain the higher capacity in inhibition of lipid peroxidation for some isoflavonones compared to flavonones and even compared to quercetin, known as the most potent antioxidant in the flavonoid family in liposome and low-density lipoproteins [27]
Epidemiological studies indicate that a high intake of carotenoids is beneficial to human health, an effect often assigned to the antioxidant activities of carotenoids [33,34,35], the molecular mechanism remains uncertain
Summary
Flavonoids and carotenoids are naturally occurring pigments ubiquitously present in the plant kingdom and in other types of photosynthetic organisms, playing important roles in light harvesting, photo-protection and antioxidation [1,2]. They are exogenous antioxidant compounds for animals and humans through daily consumption of a diet of grains, vegetables and fruits [3,4,5,6,7]. A discussion of the future trend along this research line will be given (Section 4)
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